Herbicidal compounds

ABSTRACT

The present invention relates to compounds of Formula (I), (I) wherein R 1 , R 2 , R 3  and R 4  are as defined herein. The invention further relates to herbicidal compositions which comprise a compound of Formula (I), to their use for controlling weeds, in particular in crops of useful plants.

The present invention relates to novel herbicidal cyclohexanedionecompounds, to processes for their preparation, to herbicidalcompositions which comprise the novel compounds, and to their use forcontrolling weeds.

Herbicidal cyclic dione compounds substituted by a phenyl which hasvarious substituents are disclosed in, for example, WO2008/110308,WO2014/096289 and WO2015/197468. The present invention relates to novelherbicidal cyclohexanedione derivatives with improved properties.

Thus, according to the present invention there is provided a compound ofFormula (I)

-   -   wherein    -   R¹ is selected from methyl, ethynyl, 1-propynyl, phenyl and a 5        or 6 membered heteroaryl which comprises one or two nitrogen        heteroatoms, said phenyl and heteroaryl optionally substituted        by one or two R¹⁵ substituents;    -   R² is methyl, ethyl, methoxy or chloro;    -   R³ is selected from the group consisting of methyl, ethyl,        methoxy and chloro;    -   R⁴ is selected from the group consisting of D1, D2, D3, D4, D5,        D6, D7, D8, D9, D10, D11, D12, D13, D14, D15, D16, D17, D18,        D19, D20, D21 D22, D23, D24, D25, D26, D27, D28, D29, D30, D31,        D32, D33, D34, D35 and D36:

-   -   Y is selected from the group consisting of O, CR²⁷R²⁸ and N—R²⁹;    -   Z is N or CH;    -   R^(4c) is selected from the group consisting of hydrogen,        C₁-C₄alkyl, C₁-C₄alkoxy-, C₁-C₄haloalkyl, —C(═O)C₁-C₄alkyl,        —C(═O)C₁-C₄haloalkyl, —S(O)_(n)C₁-C₆alkyl,        —S(O)_(n)C₁-C₆haloalkyl, —S(O)_(n)—(CH₂)_(n)—C₃-C₆cycloalkyl,        —S(O)_(n)C(R¹¹)R¹²R¹³, —C(O)H, —C(O)—(CH₂)_(n)—C₃-C₆cycloalkyl,        —C(O)C(R¹¹)R¹²R¹³, —C(O)C₂-C₄alkenyl, —C(O)(CR⁹R¹⁰)CN,        —C(O)(CR⁹R¹⁰)(CR⁹R¹⁰)CN, —C(O)CH₂C(O)—C₁-C₆alkyl,        —C(O)CH₂OC(O)—C₁-C₆alkyl, —C(O)OC₁-C₆alkyl,        —C(O)OC₁-C₆haloalkyl, —C(O)(CH₂)_(n)S(O)_(n)C₁-C₆alkyl,        —C(O)C₁-C₃alkoxyC₁-C₆alkyl, —C(O)C₁-C₃alkoxyC₂-C₆alkenyl,        —C(O)C₁-C₃alkoxyC₂-C₆alkynyl, —C(O)C₁-C₃alkoxyC₁-C₆haloalkyl,        —C(O)C₁-C₃alkoxyC₃-C₆cycloalkyl, —C(O)OC₁-C₃alkoxyC₁-C₆alkyl,        —C(O)C₁-C₃alkoxyC₁-C₃alkoxyC₁-C₆alkyl, —C(O)(CH₂)_(n)NR⁵R⁶,        —C(O)—(CH₂)_(n)—NR⁷C(O)R⁸, —C(O)—(CH₂)_(n)—O—N═CR⁵R⁵, —CN,        —S(O)₂NR¹⁶R¹⁷, —S(O)(═NR¹⁸)R¹⁹, —C(O)C(O)R²⁰,        —C(O)C(R²³)═N—O—R²⁴ or —C(O)C(R²³)═N—NR²⁵R²⁶, —(CH₂)_(n)-phenyl,        —C(O)—(CH₂)_(n)-phenyl, —S(O)_(n)—(CH₂)_(n)-phenyl,        -heterocyclyl, —C(O)—(CH₂)_(n)-heterocyclyl,        —C(O)(CH₂)_(n)O—(CH₂)_(n)-heterocyclyl,        —S(O)_(n)—(CH₂)_(n)-heterocyclyl, wherein each heterocyclyl is a        5- or 6-membered heterocyclyl which may be aromatic, saturated        or partially saturated and can contain from 1 to 4 heteroatoms        each independently selected from the group consisting of oxygen,        nitrogen and sulphur, and wherein said heterocyclyl or phenyl        groups are optionally substituted by one, two or three        substituents independently selected from the group consisting of        C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₂-C₃alkenyl,        C₂-C₃alkynyl, halogen, cyano and nitro;    -   R⁵ is selected from the group consisting of hydrogen and C₁-C₆        alkyl;    -   R⁶ is selected from the group consisting of hydrogen,        C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₁-C₆haloalkyl,        hydroxyl-, C₁-C₆alkoxy, C₃-C₆ cycloalkyl,        —C₁-C₄alkoxyC₁-C₆alkyl, —C₁-C₃alkoxyC₁-C₆haloalkyl,        —(CR⁹R¹⁰)C₁-C₆haloalkyl, —(CR⁹R¹⁰)C(O)NR⁵R⁵, phenyl, -pyridyl,        wherein the phenyl and pyridyl are optionally substituted by        one, two or three substituents independently selected from the        group consisting of C₁-C₃ alkyl, C₁-C₃ haloalkyl, C₁-C₃ alkoxy,        C₂-C₃ alkenyl, C₂-C₃ alkynyl, halogen, cyano and nitro; or    -   R⁵ and R⁶ together form —CH₂CH₂OCH₂CH₂—; and    -   R⁷ is selected from the group consisting of hydrogen and C₁-C₆        alkyl;    -   R⁸ is selected from the group consisting of hydrogen, C₁-C₆        alkyl, C₁-C₆ alkoxy, C₃-C₆ cycloalkyl, phenyl, -pyridyl, wherein        the phenyl and pyridyl are optionally substituted by one, two or        three substituents independently selected from the group        consisting of C₁-C₃ alkyl, C₁-C₃ haloalkyl, C₁-C₃ alkoxy, C₂-C₃        alkenyl, C₂-C₃ alkynyl, halogen, cyano and nitro;    -   R⁹ is hydrogen or methyl;    -   R¹⁰ is hydrogen or methyl; or    -   R⁹ and R¹⁰ together form —CH₂CH₂—; and    -   R¹¹ is hydrogen or methyl;    -   R¹² is selected from the group consisting of hydrogen, C₁-C₆        alkyl, hydroxyl and C₁-C₆ alkoxy-;    -   R¹³ is selected from the group consisting of hydrogen, C₁-C₆        alkyl, hydroxyl and C₁-C₆ alkoxy; or    -   R¹² and R¹³ together form —CH₂—X—CH₂—; and    -   X is selected from the group consisting of O, S and N—R¹⁴;    -   R¹⁴ is selected from the group consisting of hydrogen, C₁-C₃        alkyl and C₁-C₃ alkoxy-;    -   R¹⁵ is independently selected from the group consisting of C₁-C₄        alkyl, C₁-C₄ haloalkyl, cyano and halogen;    -   R¹⁶ is hydrogen or C₁-C₅alkyl; and    -   R¹⁷ is selected from the group consisting of hydrogen,        C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₆ alkoxy-C₁-C₃alkyl-,        —C(O)C₁-C₆alkyl, —C(O)OC₁-C₆alkyl and CH₂CN; or    -   R¹⁶ and R¹⁷ together form —CH₂CH₂OCH₂CH₂—, —CH₂CH₂S(O)₂CH₂CH₂—;    -   R¹⁸ is hydrogen or C₁-C₆alkyl;    -   R¹⁹ is selected from the group consisting of hydrogen, C₁-C₆        alkyl, C₁-C₆ alkoxy, C₃-C₆cycloalkyl, phenyl, -pyridyl, wherein        the phenyl and pyridyl are optionally substituted by one, two or        three substituents independently selected from the group        consisting of C₁-C₃ alkyl, C₁-C₃ haloalkyl, C₁-C₃ alkoxy, C₂-C₃        alkenyl, C₂-C₃ alkynyl, halogen, cyano and nitro;    -   R²⁰ is selected from the group consisting of C₁-C₆alkyl,        C₁-C₆haloalkyl, C₁-C₆alkoxy-, C₁-C₆haloalkoxy, —NR²¹R²², phenyl        and -pyridyl, wherein the phenyl and pyridyl are optionally        substituted by one, two or three substituents independently        selected from the group consisting of C₁-C₃ alkyl, C₁-C₃        haloalkyl, C₁-C₃ alkoxy, C₂-C₃ alkenyl, C₂-C₃ alkynyl, halogen,        cyano and nitro;    -   R²¹ is selected from the group consisting of hydrogen, C₁-C₆        alkyl, C₁-C₆ alkoxy, C₁-C₆alkoxyC₁-C₃alkyl-, C₃-C₆ cycloalkyl,        C₁-C₆haloalkyl- and C₁-C₆haloalkoxy-, —C(O)C₁-C₆alkyl, phenyl,        -pyridyl, wherein the phenyl and pyridyl are optionally        substituted by one, two or three substituents independently        selected from the group consisting of C₁-C₃ alkyl, C₁-C₃        haloalkyl, C₁-C₃ alkoxy, C₂-C₃ alkenyl, C₂-C₃ alkynyl, halogen,        cyano and nitro;    -   R²² is hydrogen or C₁-C₆alkyl; or    -   R²¹ and R²² together form —CH₂CH₂OCH₂CH₂—;    -   R²³ is selected from the group consisting of hydrogen,        C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy- and C₁-C₆haloalkoxy-;    -   R²⁴ is selected from the group consisting of hydrogen,        C₁-C₆alkyl, C₁-C₆alkoxyC₁-C₃alkyl-, C₃-C₆cycloalkyl, —CH₂CN,        tetrahydropyranyl-, phenyl and -pyridyl, wherein the phenyl and        pyridyl are optionally substituted by one, two or three        substituents independently selected from the group consisting of        C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₂-C₃alkenyl,        C₂-C₃alkynyl, halogen, cyano and nitro;    -   R²⁵ is hydrogen or C₁-C₆ alkyl;    -   R²⁶ is hydrogen or C₁-C₆ alkyl;    -   R²⁷ is hydrogen or C₁-C₄alkyl;    -   R²⁸ is hydrogen or C₁-C₄alkyl;    -   R²⁹ is selected from the group consisting of hydrogen,        C₁-C₄alkyl, C₁-C₄alkoxy-, C₁-C₄haloalkyl, —C(═O)C₁-C₄alkyl,        —C(═O)C₁-C₄haloalkyl; and    -   R³⁰ and R³¹ are independently selected from the group consisting        of hydrogen, halogen, C₁-C³ alkyl, C₁-C₃ haloalkyl and        C₁-C₃alkoxy but wherein both R³⁰ and R³¹ are not hydrogen;    -   G is selected from the group consisting of hydrogen,        —(CH₂)_(n)—R^(a), —C(O)—R^(a), —C(O)—(CR^(c)R^(d))_(n)—O—R^(b),        —C(O)—(CR^(c)R^(d))_(n)—S—R^(b), —C(O)NR^(a)R^(a), —S(O)₂—R^(a)        and C₁-C₈alkoxy-C₁-C₃alkyl-;    -   R^(a) is independently selected from the group consisting of        hydrogen, C₁-C₈alkyl, C₁-C₃haloalkyl, C₂-C₈alkenyl,        C₂-C₈alkynyl, C₃-C₆cycloalkyl, heterocyclyl and phenyl wherein        said heterocyclyl and phenyl groups are optionally substituted        by one, two or three substituents independently selected from        the group consisting of C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy,        C₂-C₃alkenyl, C₂-C₃alkynyl, halogen, cyano and nitro;    -   R^(b) is selected from the group consisting of C₁-C₈alkyl,        C₁-C₃haloalkyl, C₂-C₈alkenyl, C₂-C₈alkynyl, C₃-C₆ cycloalkyl,        heterocyclyl and phenyl wherein said heterocyclyl and phenyl        groups are optionally substituted by one, two or three        substituents independently selected from the group consisting of        C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₂-C₃alkenyl,        C₂-C₃alkynyl, halogen, cyano and nitro;    -   R^(c) is hydrogen or C₁-C₃ alkyl;    -   R^(d) is hydrogen or C₁-C₃ alkyl; and    -   n is independently 0, 1 or 2;    -   or an agriculturally acceptable salt thereof.

Alkyl groups (e.g C₁-C₆alkyl) include, for example, methyl (Me, CH₃),ethyl (Et, C₂H₅), n-propyl (n-Pr), isopropyl (i-Pr), n-butyl (n-Bu),isobutyl (i-Bu), sec-butyl (s-Bu) and tert-butyl (t-Bu).

Alkenyl and alkynyl moieties can be in the form of straight or branchedchains, and the alkenyl moieties, where appropriate, can be of eitherthe (E)- or (Z)-configuration. Examples are vinyl, allyl and propargyl.Alkenyl and alkynyl moieties can contain one or more double and/ortriple bonds in any combination.

Halogen (or halo) encompasses fluorine, chlorine, bromine or iodine. Thesame correspondingly applies to halogen in the context of otherdefinitions, such as haloalkyl.

Haloalkyl groups (e.g C₁-C₆haloalkyl) are, for example, fluoromethyl,difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl,trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl,pentafluoroethyl, 1,1-difluoro-2,2,2-trichloroethyl,2,2,3,3-tetrafluoroethyl and 2,2,2-trichloroethyl, heptafluoro-n-propyland perfluoro-n-hexyl.

Alkoxy groups (e.g C₁-C₄alkoxy-) are, for example, methoxy, ethoxy,propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy or tert-butoxy,preferably methoxy and ethoxy.

Alkoxyalkyl groups (e.g C₁-C₆alkoxy-C₁-C₃alkyl-) includes, for example,methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, n-propoxymethyl,n-propoxyethyl, isopropoxymethyl or isopropoxyethyl.

Cycloalkyl groups (e.g C₃-C₆cycloalkyl-) include, for examplecyclopropyl (c-propyl, c-Pr), cyclobutyl (c-butyl, c-Bu), cyclopentyl(c-pentyl) and cyclohexyl (c-hexyl) and may be substituted orunsubstituted as indicated.

C₁-C₆alkyl-S— (alkylthio) is, for example, methylthio, ethylthio,propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio ortert-butylthio, preferably methylthio or ethylthio.

C₁-C₆alkyl-S(O)— (alkylsulfinyl) is, for example, methylsulfinyl,ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl,isobutylsulfinyl, sec-butylsulfinyl or tert-butylsulfinyl, preferablymethylsulfinyl or ethylsulfinyl.

C₁-C₆alkyl-S(O)₂— (alkylsulfonyl) is, for example, methylsulfonyl,ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl,isobutylsulfonyl, sec-butylsulfonyl or tert-butylsulfonyl, preferablymethylsulfonyl or ethylsulfonyl.

Heterocyclyl, unless stated otherwise, is a 5- or 6-memberedheterocyclyl which may be aromatic, saturated or partially saturated andcan contain from 1 to 4 heteroatoms each independently selected from thegroup consisting of oxygen, nitrogen and sulphur.

The invention also relates agriculturally acceptable salts of thecompounds of Formula (I). Such salts include those which are able toform with amines, alkali metal and alkaline earth metal bases orquaternary ammonium bases. Among the alkali metal and alkaline earthmetal hydroxides as salt formers, special mention should be made of thehydroxides of lithium, sodium, potassium, magnesium and calcium, butespecially the hydroxides of sodium and potassium. The compounds ofFormula (I) according to the invention also include hydrates which maybe formed during the salt formation.

Examples of amines suitable for ammonium salt formation include ammoniaas well as primary, secondary and tertiary C₁-C₁₃alkylamines,C₁-C₄hydroxyalkylamines and C₂-C₄alkoxyalkylamines, for examplemethylamine, ethylamine, n-propylamine, isopropylamine, the fourbutylamine isomers, n-amylamine, isoamylamine, hexylamine, heptylamine,octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine,heptadecylamine, octadecylamine, methylethylamine, methylisopropylamine,methylhexylamine, methylnonylamine, methylpentadecylamine,methyloctadecylamine, ethylbutylamine, ethylheptylamine,ethyloctylamine, hexylheptylamine, hexyloctylamine, dimethylamine,diethylamine, di-n-propylamine, diisopropylamine, di-n-butylamine,di-n-amylamine, diisoamylamine, dihexylamine, diheptylamine,dioctylamine, ethanolamine, n-propanolamine, isopropanolamine,N,N-diethanolamine, N-ethylpropanolamine, N-butylethanolamine,allylamine, n-but-2-enylamine, n-pent-2-enylamine,2,3-dimethylbut-2-enylamine, dibut-2-enylamine, n-hex-2-enylamine,propylenediamine, trimethylamine, triethylamine, tri-n-propylamine,triisopropylamine, tri-n-butylamine, triisobutylamine,tri-sec-butylamine, tri-n-amylamine, methoxyethylamine andethoxyethylamine; heterocyclic amines, for example pyridine, quinoline,isoquinoline, morpholine, piperidine, pyrrolidine, indoline,quinuclidine and azepine; primary arylamines, for example anilines,methoxyanilines, ethoxyanilines, o-, m- and p-toluidines,phenylenediamines, benzidines, naphthylamines and o-, m- andp-chloroanilines; but especially triethylamine, isopropylamine anddiisopropylamine.

In one embodiment of the present invention R¹ is 1-propynyl.

In another embodiment of the present invention R¹ is phenyl optionallysubstituted by one or two R¹⁵ substituents, e.g selected from the groupconsisting of cyano, chloro and fluoro.

In another embodiment of the present invention R¹ is a 5 or 6 memberedheteroaryl which comprises one or two nitrogen heteroatoms, saidheteroaryl optionally substituted by one or two R¹⁵ substituents, e.gselected from the group consisting of cyano, chloro and fluoro. In apreferred embodiment, said heteroaryl is selected from the groupconsisting of pyridyl, pyrimidinyl, and pyrazolyl.

In one embodiment of the present invention R² is preferably methyl.

In one embodiment of the present invention R³ is preferably methyl.

In one embodiment of the present invention R⁴ is selected from the groupconsisting of D1, D2, D3, D4, D5, D6, D7, D8, D9, D10, D11, D12, D13,D14, D15, D16, D17, D18, D19, D20, D21 D22, D23, D24, D25, D26, D27,D28, D29, D30, D31, D32 and D33

In one embodiment of the present invention R⁴ is preferably selectedfrom the group consisting of D4, D5, D6, D12, D13, D14, D23, D28 andD30.

In more preferred embodiment of the present invention R⁴ is D4 or D6.

In one embodiment of the present invention, R^(4c) is preferablyC₁-C₂alkoxy-(e.g methoxy or ethoxy).

In another embodiment of the present invention R^(4c) is preferably—C(═O)C₁-C₃alkyl (e.g —C(C═O)methyl, —C(C═O)ethyl, —C(C═O)i-propyl).

In another embodiment of the present invention, R^(4c) is—C(═O)C₁-C₃haloalkyl, more preferably —C(═O)C₁-C₂fluoroalkyl e.g—C(═O)CH₂F, —C(═O)CHF₂, —C(═O)CF₃).

In one embodiment of the present invention, R^(4c) is—S(O)_(n)C₁-C₆alkyl especially —S(O)₂methyl or —S(O)₂ethyl

In another embodiment R^(4c) is —S(O)_(n)C₁-C₆haloalkyl, for example—S(O)₂chloromethyl.

In another embodiment R^(4c) is —S(O)_(n)—(CH₂)_(n)—C₃-C₆cycloalkyl, forexample —S(O)₂—(CH₂)-c-propyl.

In another embodiment of the present invention, R^(4c) is—C(O)OC₁-C₆alkyl, especially —C(O)—O-methyl.

In another embodiment of the present invention, R^(4c) is—S(O)_(n)C(R¹¹)R¹²R¹³ or —C(O)C(R¹¹)R¹²R¹³ wherein R¹¹ is hydrogen ormethyl and R¹²R¹³ taken together are —CH₂OCH₂— (oxetan-3-yl).

In another embodiment of the present invention, R^(4c) is—C(O)—(CH₂)_(n)—C₃-C₆cycloalkyl, for example —C(O)-c-propyl or—C(O)—(CH₂)-c-propyl.

In another embodiment of the present invention, R^(4c) is—C(O)(CR⁹R¹⁰)CN, for example —C(O)CH₂CN, —C(O)CH(CH₃)CN or—C(O)C(CH₃)₂CN.

In another embodiment of the present invention, R^(4c) is—C(O)(CH₂)_(n)S(O)_(n)C₁-C₆alkyl, for example —C(O)CH₂S(O)₂methyl.

In another embodiment of the present invention, R^(4c) is—C(O)C₁-C₃alkoxyC₁-C₆alkyl, for example —C(O)CH₂CH₂—O—CH₃ or—C(O)CH(CH₃)—O—CH₃.

In another embodiment of the present invention, R^(4c) is —C(O)NR⁵R⁶,especially wherein R⁵ is hydrogen and R⁶ is C₁-C₆ alkyl e.g t-butyl.

In another embodiment of the present invention, R^(4c) is—C(O)—(CH₂)_(n)—NR⁷C(O)R⁸, for example —C(O)—(CH₂)—NR⁷C(O)R⁸ or—C(O)NR⁷C(O)R⁸, for example —C(O)NHC(O)-t-butyl.

In another embodiment of the present invention, R^(4c) is selected fromthe group consisting of -phenyl, —C(O)-phenyl, —S(O)_(n)phenyl whereineach phenyl is optionally substituted as defined previously.

In another embodiment of the present invention R^(4c) is heterocyclyl,—C(O)— heterocyclyl or —S(O)_(n)-heterocyclyl. In another embodiment,each aforementioned heterocyclyl is an aromatic heterocyclyl (i.eheteroaryl), more preferably selected from the group consisting offuranyl, pyrrolyl, thiophenyl, imidazolyl, pyrazolyl, oxazolyl,isoxazolyl, thiazolyl, pyranyl, pyridyl, pyrazinyl, pyrimidinyl,pyridazinyl, and triazolyl more preferably selected from the groupconsisting of pyridyl, pyridazinyl, pyrimidinyl and pyrazinyl each ofwhich is optionally substituted as defined previously. In anotherembodiment, each aforementioned heterocyclyl is a partially saturatedheterocyclyl, more preferably selected from the group consisting ofimidazolinyl, isoxazolinyl and thiazolinyl each of which is optionallysubstituted as defined previously. In another embodiment, eachaforementioned heterocyclyl is a saturated heterocyclyl more preferablyselected from the group consisting of morpholinyl, tetrahydrofuryl andtetrahydropyranyl each of which is optionally substituted as definedpreviously.

In a preferred embodiment of the present invention R^(4c) is selectedfrom the group consisting of —C(═O)C₁-C₄alkyl, —S(O)_(n)C₁-C₆alkyl,—C(O)C₁-C₃alkoxyC₁-C₆alkyl and —C(═O)phenyl.

In one embodiment of the present invention, G is selected from the groupconsisting of hydrogen, C₁-C₆alkyl (e.g methyl, ethyl, n-propyl,i-propyl, n-butyl, t-butyl, —C₂-C₈alkenyl (e.g vinyl), C₂-C₈alkynyl (e.gpropargyl), —C(O)C₁-C₈alkyl (more preferably —C(O)C₁-C₆alkyl e.g—C(O)i-propyl and —C(O)t-butyl) and —C(O)—O—C₁-C₈alkyl (more preferably—C(O)—O—C₁-C₆alkyl e.g —C(O)—O-methyl). In a preferred embodiment, G ishydrogen.

Depending on the nature of the substituents, compounds of Formula (I)may exist in different isomeric forms. When G is hydrogen, for example,compounds of Formula (I) may exist in different tautomeric forms.

This invention covers all such isomers and tautomers and mixturesthereof in all proportions. Also, when substituents contain doublebonds, cis- and trans-isomers can exist. These isomers, too, are withinthe scope of the claimed compounds of the Formula (I). Compounds ofFormula (I) may contain asymmetric centres and may be present as asingle enantiomer, pairs of enantiomers in any proportion or, where morethan one asymmetric centre are present, contain diastereoisomers in allpossible ratios. Typically one of the enantiomers has enhancedbiological activity compared to the other possibilities.

The compounds of Formula (I) according to the invention can be used asherbicides by themselves, but they are generally formulated intoherbicidal compositions using formulation adjuvants, such as carriers,solvents and surface-active agents (SFAs). Thus, the present inventionfurther provides a herbicidal composition comprising a herbicidalcompound according to any one of the previous claims and anagriculturally acceptable formulation adjuvant. The composition can bein the form of concentrates which are diluted prior to use, althoughready-to-use compositions can also be made. The final dilution isusually made with water, but can be made instead of, or in addition to,water, with, for example, liquid fertilisers, micronutrients, biologicalorganisms, oil or solvents.

The herbicidal compositions generally comprise from 0.1 to 99% byweight, especially from 0.1 to 95% by weight, compounds of Formula (I)and from 1 to 99.9% by weight of a formulation adjuvant which preferablyincludes from 0 to 25% by weight of a surface-active substance.

The compositions can be chosen from a number of formulation types, manyof which are known from the Manual on Development and Use of FAOSpecifications for Plant Protection Products, 5th Edition, 1999. Theseinclude dustable powders (DP), soluble powders (SP), water solublegranules (SG), water dispersible granules (WG), wettable powders (WP),granules (GR) (slow or fast release), soluble concentrates (SL), oilmiscible liquids (OL), ultra low volume liquids (UL), emulsifiableconcentrates (EC), dispersible concentrates (DC), emulsions (both oil inwater (EW) and water in oil (EO)), micro-emulsions (ME), suspensionconcentrates (SC), aerosols, capsule suspensions (CS) and seed treatmentformulations. The formulation type chosen in any instance will dependupon the particular purpose envisaged and the physical, chemical andbiological properties of the compound of Formula (I).

Dustable powders (DP) may be prepared by mixing a compound of Formula(I) with one or more solid diluents (for example natural clays, kaolin,pyrophyllite, bentonite, alumina, montmorillonite, kieselguhr, chalk,diatomaceous earths, calcium phosphates, calcium and magnesiumcarbonates, sulphur, lime, flours, talc and other organic and inorganicsolid carriers) and mechanically grinding the mixture to a fine powder.

Soluble powders (SP) may be prepared by mixing a compound of Formula (I)with one or more water-soluble inorganic salts (such as sodiumbicarbonate, sodium carbonate or magnesium sulphate) or one or morewater-soluble organic solids (such as a polysaccharide) and, optionally,one or more wetting agents, one or more dispersing agents or a mixtureof said agents to improve water dispersibility/solubility. The mixtureis then ground to a fine powder. Similar compositions may also begranulated to form water soluble granules (SG).

Wettable powders (WP) may be prepared by mixing a compound of Formula(I) with one or more solid diluents or carriers, one or more wettingagents and, preferably, one or more dispersing agents and, optionally,one or more suspending agents to facilitate the dispersion in liquids.The mixture is then ground to a fine powder. Similar compositions mayalso be granulated to form water dispersible granules (WG).

Granules (GR) may be formed either by granulating a mixture of acompound of Formula (I) and one or more powdered solid diluents orcarriers, or from pre-formed blank granules by absorbing a compound ofFormula (I) (or a solution thereof, in a suitable agent) in a porousgranular material (such as pumice, attapulgite clays, fuller's earth,kieselguhr, diatomaceous earths or ground corn cobs) or by adsorbing acompound of Formula (I) (or a solution thereof, in a suitable agent) onto a hard core material (such as sands, silicates, mineral carbonates,sulphates or phosphates) and drying if necessary. Agents which arecommonly used to aid absorption or adsorption include solvents (such asaliphatic and aromatic petroleum solvents, alcohols, ethers, ketones andesters) and sticking agents (such as polyvinyl acetates, polyvinylalcohols, dextrins, sugars and vegetable oils). One or more otheradditives may also be included in granules (for example an emulsifyingagent, wetting agent or dispersing agent).

Dispersible Concentrates (DC) may be prepared by dissolving a compoundof Formula (I) in water or an organic solvent, such as a ketone, alcoholor glycol ether. These solutions may contain a surface active agent (forexample to improve water dilution or prevent crystallisation in a spraytank).

Emulsifiable concentrates (EC) or oil-in-water emulsions (EW) may beprepared by dissolving a compound of Formula (I) in an organic solvent(optionally containing one or more wetting agents, one or moreemulsifying agents or a mixture of said agents). Suitable organicsolvents for use in ECs include aromatic hydrocarbons (such asalkylbenzenes or alkylnaphthalenes, exemplified by SOLVESSO 100,SOLVESSO 150 and SOLVESSO 200; SOLVESSO is a Registered Trade Mark),ketones (such as cyclohexanone or methylcyclohexanone) and alcohols(such as benzyl alcohol, furfuryl alcohol or butanol),N-alkylpyrrolidones (such as N-methylpyrrolidone or N-octylpyrrolidone),dimethyl amides of fatty acids (such as C₈-C₁₀ fatty acid dimethylamide)and chlorinated hydrocarbons. An EC product may spontaneously emulsifyon addition to water, to produce an emulsion with sufficient stabilityto allow spray application through appropriate equipment.

Preparation of an EW involves obtaining a compound of Formula (I) eitheras a liquid (if it is not a liquid at room temperature, it may be meltedat a reasonable temperature, typically below 70° C.) or in solution (bydissolving it in an appropriate solvent) and then emulsifying theresultant liquid or solution into water containing one or more SFAs,under high shear, to produce an emulsion. Suitable solvents for use inEWs include vegetable oils, chlorinated hydrocarbons (such aschlorobenzenes), aromatic solvents (such as alkylbenzenes oralkylnaphthalenes) and other appropriate organic solvents which have alow solubility in water.

Microemulsions (ME) may be prepared by mixing water with a blend of oneor more solvents with one or more SFAs, to produce spontaneously athermodynamically stable isotropic liquid formulation. A compound ofFormula (I) is present initially in either the water or the solvent/SFAblend. Suitable solvents for use in MEs include those hereinbeforedescribed for use in in ECs or in EWs. An ME may be either anoil-in-water or a water-in-oil system (which system is present may bedetermined by conductivity measurements) and may be suitable for mixingwater-soluble and oil-soluble pesticides in the same formulation. An MEis suitable for dilution into water, either remaining as a microemulsionor forming a conventional oil-in-water emulsion.

Suspension concentrates (SC) may comprise aqueous or non-aqueoussuspensions of finely divided insoluble solid particles of a compound ofFormula (I). SCs may be prepared by ball or bead milling the solidcompound of Formula (I) in a suitable medium, optionally with one ormore dispersing agents, to produce a fine particle suspension of thecompound. One or more wetting agents may be included in the compositionand a suspending agent may be included to reduce the rate at which theparticles settle. Alternatively, a compound of Formula (I) may be drymilled and added to water, containing agents hereinbefore described, toproduce the desired end product.

Aerosol formulations comprise a compound of Formula (I) and a suitablepropellant (for example n-butane). A compound of Formula (I) may also bedissolved or dispersed in a suitable medium (for example water or awater miscible liquid, such as n-propanol) to provide compositions foruse in non-pressurised, hand-actuated spray pumps.

Capsule suspensions (CS) may be prepared in a manner similar to thepreparation of EW formulations but with an additional polymerisationstage such that an aqueous dispersion of oil droplets is obtained, inwhich each oil droplet is encapsulated by a polymeric shell and containsa compound of Formula (I) and, optionally, a carrier or diluenttherefor. The polymeric shell may be produced by either an interfacialpolycondensation reaction or by a coacervation procedure. Thecompositions may provide for controlled release of the compound ofFormula (I) and they may be used for seed treatment. A compound ofFormula (I) may also be formulated in a biodegradable polymeric matrixto provide a slow, controlled release of the compound.

The composition may include one or more additives to improve thebiological performance of the composition, for example by improvingwetting, retention or distribution on surfaces; resistance to rain ontreated surfaces; or uptake or mobility of a compound of Formula (I).Such additives include surface active agents (SFAs), spray additivesbased on oils, for example certain mineral oils or natural plant oils(such as soy bean and rape seed oil), and blends of these with otherbio-enhancing adjuvants (ingredients which may aid or modify the actionof a compound of Formula (I).

Wetting agents, dispersing agents and emulsifying agents may be SFAs ofthe cationic, anionic, amphoteric or non-ionic type.

Suitable SFAs of the cationic type include quaternary ammonium compounds(for example cetyltrimethyl ammonium bromide), imidazolines and aminesalts.

Suitable anionic SFAs include alkali metals salts of fatty acids, saltsof aliphatic monoesters of sulphuric acid (for example sodium laurylsulphate), salts of sulphonated aromatic compounds (for example sodiumdodecylbenzenesulphonate, calcium dodecylbenzenesulphonate,butylnaphthalene sulphonate and mixtures of sodium di-isopropyl- andtri-isopropyl-naphthalene sulphonates), ether sulphates, alcohol ethersulphates (for example sodium laureth-3-sulphate), ether carboxylates(for example sodium laureth-3-carboxylate), phosphate esters (productsfrom the reaction between one or more fatty alcohols and phosphoric acid(predominately mono-esters) or phosphorus pentoxide (predominatelydi-esters), for example the reaction between lauryl alcohol andtetraphosphoric acid; additionally these products may be ethoxylated),sulphosuccinamates, paraffin or olefine sulphonates, taurates andlignosulphonates.

Suitable SFAs of the amphoteric type include betaines, propionates andglycinates.

Suitable SFAs of the non-ionic type include condensation products ofalkylene oxides, such as ethylene oxide, propylene oxide, butylene oxideor mixtures thereof, with fatty alcohols (such as oleyl alcohol or cetylalcohol) or with alkylphenols (such as octylphenol, nonylphenol oroctylcresol); partial esters derived from long chain fatty acids orhexitol anhydrides; condensation products of said partial esters withethylene oxide; block polymers (comprising ethylene oxide and propyleneoxide); alkanolamides; simple esters (for example fatty acidpolyethylene glycol esters); amine oxides (for example lauryl dimethylamine oxide); and lecithins.

Suitable suspending agents include hydrophilic colloids (such aspolysaccharides, polyvinylpyrrolidone or sodium carboxymethylcellulose)and swelling clays (such as bentonite or attapulgite).

The herbicidal compounds of the present invention can also be used inmixture with one or more additional herbicides and/or plant growthregulators. Examples of such additional herbicides or plant growthregulators include acetochlor, acifluorfen (includingacifluorfen-sodium), aclonifen, ametryn, amicarbazone, aminopyralid,aminotriazole, atrazine, beflubutamid-M, bensulfuron (includingbensulfuron-methyl), bentazone, bicyclopyrone, bilanafos,bispyribac-sodium, bixlozone, bromacil, bromoxynil, butachlor,butafenacil, carfentrazone (including carfentrazone-ethyl), cloransulam(including cloransulam-methyl), chlorimuron (includingchlorimuron-ethyl), chlorotoluron, chlorsulfuron, cinmethylin, clacyfos,clethodim, clodinafop (including clodinafop-propargyl), clomazone,clopyralid, cyclopyranil, cyclopyrimorate, cyclosulfamuron, cyhalofop(including cyhalofop-butyl), 2,4-D (including the choline salt and2-ethylhexyl ester thereof), 2,4-DB, desmedipham, dicamba (including thealuminium, aminopropyl, bis-aminopropylmethyl, choline, dichloroprop,diglycolamine, dimethylamine, dimethylammonium, potassium and sodiumsalts thereof) diclosulam, diflufenican, diflufenzopyr, dimethachlor,dimethenamid-P, diquat dibromide, diuron, epyrifenacil, ethalfluralin,ethofumesate, fenoxaprop (including fenoxaprop-P-ethyl), fenoxasulfone,fenquinotrione, fentrazamide, flazasulfuron, florasulam, florpyrauxifen(including florpyrauxifen-benzyl), fluazifop (includingfluazifop-P-butyl), flucarbazone (including flucarbazone-sodium),flufenacet, flumetsulam, flumioxazin, fluometuron, flupyrsulfuron(including flupyrsulfuron-methyl-sodium), fluroxypyr (includingfluroxypyr-meptyl), fomesafen, foramsulfuron, glufosinate (including theammonium salt thereof), glyphosate (including the diammonium,isopropylammonium and potassium salts thereof), halauxifen (includinghalauxifen-methyl), haloxyfop (including haloxyfop-methyl), hexazinone,hydantocidin, imazamox, imazapic, imazapyr, imazethapyr, indaziflam,iodosulfuron (including iodosulfuron-methyl-sodium), iofensulfuron(including iofensulfuron-sodium), ioxynil, isoproturon, isoxaflutole,lancotrione, MCPA, MCPB, mecoprop-P, mesosulfuron (includingmesosulfuron-methyl), mesotrione, metamitron, metazachlor, methiozolin,metolachlor, metosulam, metribuzin, metsulfuron, napropamide,nicosulfuron, norflurazon, oxadiazon, oxasulfuron, oxyfluorfen, paraquatdichloride, pendimethalin, penoxsulam, phenmedipham, picloram,pinoxaden, pretilachlor, primisulfuron-methyl, prometryne, propanil,propaquizafop, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron,pyraclonil, pyraflufen (including pyraflufen-ethyl), pyrasulfotole,pyridate, pyriftalid, pyrimisulfan, pyroxasulfone, pyroxsulam,quinclorac, quinmerac, quizalofop (including quizalofop-P-ethyl andquizalofop-P-tefuryl), rimsulfuron, saflufenacil, sethoxydim, simazine,S-metalochlor, sulfentrazone, sulfosulfuron, tebuthiuron, tefuryltrione,tembotrione, terbuthylazine, terbutryn, tetflupyrolimet, thiencarbazone,thifensulfuron, tiafenacil, tolpyralate, topramezone, tralkoxydim,triafamone, triallate, triasulfuron, tribenuron (includingtribenuron-methyl), triclopyr, trifloxysulfuron (includingtrifloxysulfuron-sodium), trifludimoxazin, trifluralin, triflusulfuron,3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydropyrimidin-1(2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylicacid ethyl ester,4-hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one,4-hydroxy-1,5-dimethyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one,5-ethoxy-4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one,4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one,4-hydroxy-1,5-dimethyl-3-[1-methyl-5-(trifluoromethyl)pyrazol-3-yl]imidazolidin-2-one,(4R)1-(5-tert-butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imidazolidin-2-one,3-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxo-pyridazine-4-carbonyl]bicyclo[3.2.1]octane-2,4-dione,2-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxo-pyridazine-4-carbonyl]-5-methyl-cyclohexane-1,3-dione,2-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxo-pyridazine-4-carbonyl]cyclohexane-1,3-dione,2-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxo-pyridazine-4-carbonyl]-5,5-dimethyl-cyclohexane-1,3-dione,6-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxo-pyridazine-4-carbonyl]-2,2,4,4-tetramethyl-cyclohexane-1,3,5-trione,2-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxo-pyridazine-4-carbonyl]-5-ethyl-cyclohexane-1,3-dione,2-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxo-pyridazine-4-carbonyl]-4,4,6,6-tetramethyl-cyclohexane-1,3-dione,2-[6-cyclopropyl-2-(3,4-dimethoxyphenyl)-3-oxo-pyridazine-4-carbonyl]-5-methyl-cyclohexane-1,3-dione,3-[6-cyclopropyl-2-(3,4-dimethoxyphenyl)-3-oxo-pyridazine-4-carbonyl]bicyclo[3.2.1]octane-2,4-dione,2-[6-cyclopropyl-2-(3,4-dimethoxyphenyl)-3-oxo-pyridazine-4-carbonyl]-5,5-dimethyl-cyclohexane-1,3-dione,6-[6-cyclopropyl-2-(3,4-dimethoxyphenyl)-3-oxo-pyridazine-4-carbonyl]-2,2,4,4-tetramethyl-cyclohexane-1,3,5-trione,2-[6-cyclopropyl-2-(3,4-dimethoxyphenyl)-3-oxo-pyridazine-4-carbonyl]cyclohexane-1,3-dione,4-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxo-pyridazine-4-carbonyl]-2,2,6,6-tetramethyl-tetrahydropyran-3,5-dione,4-[6-cyclopropyl-2-(3,4-dimethoxyphenyl)-3-oxo-pyridazine-4-carbonyl]-2,2,6,6-tetramethyl-tetrahydropyran-3,5-dione,4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylicacid (including agrochemically acceptable esters thereof, for example,methyl4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate,prop-2-ynyl4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylateand cyanomethyl4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate),3-ethylsulfanyl-N-(1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine-8-carboxamide,3-(isopropylsulfanylmethyl)-N-(5-methyl-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine-8-carboxamide,3-(isopropylsulfonylmethyl)-N-(5-methyl-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine-8-carboxamide,3-(ethylsulfonylmethyl)-N-(5-methyl-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine-8-carboxamide,ethyl2-[[3-[[3-chloro-5-fluoro-6-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-2-pyridyl]oxy]acetate,6-chloro-4-(2,7-dimethyl-1-naphthyl)-5-hydroxy-2-methyl-pyridazin-3-one,1-[2-chloro-6-(5-chloropyrimidin-2-yl)oxy-phenyl]-4,4,4-trifluoro-butan-1-oneand5-[2-chloro-6-(5-chloropyrimidin-2-yl)oxy-phenyl]-3-(difluoromethyl)isoxazole.

The mixing partners of the compound of Formula (I) may also be in theform of esters or salts, as mentioned e.g. in The Pesticide Manual,Sixteenth Edition, British Crop Protection Council, 2012.

The compound of Formula (I) can also be used in mixtures with otheragrochemicals such as fungicides, nematicides or insecticides, examplesof which are given in The Pesticide Manual.

The mixing ratio of the compound of Formula (I) to the mixing partner ispreferably from 1:100 to 1000:1.

The mixtures can advantageously be used in the above-mentionedformulations (in which case “active ingredient” relates to therespective mixture of compound of Formula (I) with the mixing partner).

The compounds or mixtures of the present invention can also be used incombination with one or more herbicide safeners. Examples of suchsafeners include benoxacor, cloquintocet (including cloquintocet-mexyl),cyprosulfamide, dichlormid, fenchlorazole (includingfenchlorazole-ethyl), fenclorim, fluxofenim, furilazole, isoxadifen(including isoxadifen-ethyl), mefenpyr (including mefenpyr-diethyl),metcamifen and oxabetrinil.

Particularly preferred are mixtures of a compound of Formula (I) withcyprosulfamide, isoxadifen-ethyl, cloquintocet-mexyl and/or metcamifen.

The safeners of the compound of Formula (I) may also be in the form ofesters or salts, as mentioned e.g. in The Pesticide Manual, 16^(th)Edition (BCPC), 2012. The reference to cloquintocet-mexyl also appliesto a lithium, sodium, potassium, calcium, magnesium, aluminium, iron,ammonium, quaternary ammonium, sulfonium or phosphonium salt thereof asdisclosed in WO 02/34048.

Preferably the mixing ratio of compound of Formula (I) to safener isfrom 100:1 to 1:10, especially from 20:1 to 1:1.

The mixtures can advantageously be used in the above-mentionedformulations (in which case “active ingredient” relates to therespective mixture of compound of Formula (I) with the safener).

The present invention still further provides a method of controllingweeds at a locus comprising crop plants and weeds, wherein the methodcomprises application to the locus of a weed controlling amount of acomposition according to the present invention. ‘Controlling’ meanskilling, reducing or retarding growth or preventing or reducinggermination. Generally the plants to be controlled are unwanted plants(weeds). ‘Locus’ means the area in which the plants are growing or willgrow.

The rates of application of compounds of Formula (I) may vary withinwide limits and depend on the nature of the soil, the method ofapplication (pre- or post-emergence; seed dressing; application to theseed furrow; no tillage application etc.), the crop plant, the weed(s)to be controlled, the prevailing climatic conditions, and other factorsgoverned by the method of application, the time of application and thetarget crop. The compounds of Formula (I) according to the invention aregenerally applied at a rate of from 10 to 2000 g/ha, especially from 50to 1000 g/ha.

The application is generally made by spraying the composition, typicallyby tractor mounted sprayer for large areas, but other methods such asdusting (for powders), drip or drench can also be used.

Useful plants in which the composition according to the invention can beused include crops such as cereals, for example barley and wheat,cotton, oilseed rape, sunflower, maize, rice, soybeans, sugar beet,sugar cane and turf.

Crop plants can also include trees, such as fruit trees, palm trees,coconut trees or other nuts. Also included are vines such as grapes,fruit bushes, fruit plants and vegetables.

Crops are to be understood as also including those crops which have beenrendered tolerant to herbicides or classes of herbicides (e.g. ALS-,GS-, EPSPS-, PPO-, ACCase- and HPPD-inhibitors) by conventional methodsof breeding or by genetic engineering. An example of a crop that hasbeen rendered tolerant to imidazolinones, e.g. imazamox, by conventionalmethods of breeding is Clearfield® summer rape (canola). Examples ofcrops that have been rendered tolerant to herbicides by geneticengineering methods include e.g. glyphosate- and glufosinate-resistantmaize varieties commercially available under the trade namesRoundupReady® and LibertyLink®.

Crops are also to be understood as being those which have been renderedresistant to harmful insects by genetic engineering methods, for exampleBt maize (resistant to European corn borer), Bt cotton (resistant tocotton boll weevil) and also Bt potatoes (resistant to Colorado beetle).Examples of Bt maize are the Bt 176 maize hybrids of NK® (SyngentaSeeds). The Bt toxin is a protein that is formed naturally by Bacillusthuringiensis soil bacteria. Examples of toxins, or transgenic plantsable to synthesise such toxins, are described in EP-A-451 878, EP-A-374753, WO 93/07278, WO 95/34656, WO 03/052073 and EP-A-427 529. Examplesof transgenic plants comprising one or more genes that code for aninsecticidal resistance and express one or more toxins are KnockOut®(maize), Yield Gard® (maize), NuCOTIN33B® (cotton), Bollgard® (cotton),NewLeaf® (potatoes), NatureGard® and Protexcta®. Plant crops or seedmaterial thereof can be both resistant to herbicides and, at the sametime, resistant to insect feeding (“stacked” transgenic events). Forexample, seed can have the ability to express an insecticidal Cry3protein while at the same time being tolerant to glyphosate.

Crops are also to be understood to include those which are obtained byconventional methods of breeding or genetic engineering and containso-called output traits (e.g. improved storage stability, highernutritional value and improved flavour).

Other useful plants include turf grass for example in golf-courses,lawns, parks and roadsides, or grown commercially for sod, andornamental plants such as flowers or bushes.

The compositions can be used to control unwanted plants (collectively,‘weeds’). The weeds to be controlled may be both monocotyledonousspecies, for example Agrostis, Alopecurus, Avena, Brachiaria, Bromus,Cenchrus, Cyperus, Digitaria, Echinochloa, Eleusine, Lolium, Monochoria,Rottboellia, Sagittaria, Scirpus, Setaria and Sorghum, anddicotyledonous species, for example Abutilon, Amaranthus, Ambrosia,Chenopodium, Chrysanthemum, Conyza, Galium, Ipomoea, Nasturtium, Sida,Sinapis, Solanum, Stellaria, Veronica, Viola and Xanthium. The compoundsof the present invention have been shown to exhibit particularly goodactivity against certain grass weed species, especially Lolium Perenne.Weeds can also include plants which may be considered crop plants butwhich are growing outside a crop area (‘escapes’), or which grow fromseed left over from a previous planting of a different crop(‘volunteers’). Such volunteers or escapes may be tolerant to certainother herbicides.

The compounds of the present invention can be prepared according to thefollowing schemes.

Compounds of formula (I) wherein G is other than hydrogen may beprepared by treating a compound of formula (I) wherein G is hydrogen,with a reagent G-Z, wherein G-Z is an alkylating agent such as an alkylhalide, acylating agent such as an acid chloride or anhydride,sulfonylating agent such as a sulfonyl chloride, carbamylating agentsuch as a carbamoyl chloride, or carbonating agent such as achloroformate, using known methods.

Compounds of formula (I) may be prepared by reacting an iodonium ylideof formula (A), wherein Ar is an optionally substituted phenyl group,and an aryl boronic acid of formula (B), in the presence of a suitablepalladium catalyst, a base and in a suitable solvent.

Suitable palladium catalysts are generally palladium(II) or palladium(0)complexes, for example palladium(II) dihalides, palladium(II) acetate,palladium(II) sulfate, bis(triphenylphosphine)-palladium(II) dichloride,bis(tricyclopentylphosphine)-palladium(II) dichloride,bis(tricyclohexyl-phosphine)palladium(II) dichloride,bis(dibenzylideneacetone)palladium(0) ortetrakis-(triphenylphosphine)palladium(0). The palladium catalyst canalso be prepared “in situ” from palladium(II) or palladium(0) compoundsby complexing with the desired ligands, by, for example, combining thepalladium(II) salt to be complexed, for example palladium(II) dichloride(PdCl₂) or palladium(II) acetate (Pd(OAc)₂), together with the desiredligand, for example triphenylphosphine (PPh₃), tricyclopentylphosphine,tricyclohexylphosphine, 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenylor 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl and theselected solvent, with a compound of formula (N), the arylboronic acidof formula (O), and a base. Also suitable are bidendate ligands, forexample 1,1′-bis(diphenylphosphino)ferrocene or1,2-bis(diphenylphosphino)ethane. By heating the reaction medium, thepalladium(II) complex or palladium(0) complex desired for the C—Ccoupling reaction is thus formed “in situ”, and then initiates the C—Ccoupling reaction.

The palladium catalysts are used in an amount of from 0.001 to 50 mol %,preferably in an amount of from 0.1 to 15 mol %, based on the compoundof formula (N). The reaction may also be carried out in the presence ofother additives, such as tetralkylammonium salts, for example,tetrabutylammonium bromide. Preferably the palladium catalyst ispalladium acetate, the base is lithium hydroxide and the solvent isaqueous 1,2-dimethoxyethane.

A compound of formula (A) may be prepared from a 1,3 dione compound offormula (C) by treatment with a hypervalent iodine reagent such as a(diacetoxy)iodobenzene or an iodosylbenzene and a base such as aqueoussodium carbonate, lithium hydroxide or sodium hydroxide in a solventsuch as water or an aqueous alcohol such as aqueous ethanol using knownprocedures.

Alternatively, the R¹ group may be added later in the synthetic sequenceby decarboxylative propynylation (where R¹ is propyne, or alternativeSuzuki/Stille or similar cross coupling where R¹ is phenyl orheteroaryl) such as in step 2 below.

Boronic acids can be prepared by methods such as below in Scheme 5. Forexample, a compound of formula (B) or (D) may be prepared from an arylhalide of formula (F) or (H) by known methods. For example, an arylhalide of formula (F) or (H) may be treated with an alkyl lithium oralkyl magnesium halide in a suitable solvent, preferably diethyl etheror tetrahydrofuran, at a temperature of between −80° C. and 30° C., andthe aryl magnesium or aryl lithium reagent obtained may then be reactedwith a trialkyl borate (preferably trimethylborate) to give an aryldialkylboronate which may be hydrolysed to provide a boronic acid offormula (B) or (D) under acidic conditions.

Compounds of formula (I) can also be prepared via Pb coupling as shownin the scheme below by reacting a compound of formula (D), to form anorganolead reagent of formula (J) and subsequent reaction with 1,3 dione(C) under conditions described, for example, by J. Pinhey, Pure andAppl. Chem., (1996), 68 (4), 819 and by M. Moloney et al., TetrahedronLett., (2002), 43, 3407. A suitable triarylbismuth compound underconditions described, for example, by A. Yu. Fedorov et al., Russ. Chem.Bull. Int. Ed., (2005), 54 (11), 2602, and by P. Koech and M. Krische,J. Am. Chem. Soc., (2004), 126 (17), 5350 and references therein may beused as a related procedure.

The compounds of type (1) can also be prepared via palladium coupling asshown in the scheme below, where boronic acid of type (B) is coupled tothe suitably protected halo-alkene of type (K) in a Suzuki typecoupling.

With suitable conditions, a suitable 1,3 dione may also be directlycoupled to a Halo-compound (for example of formula (L)) with palladiumcatalysis. Propynylation or arylation/Heteroarylation of intermediate(M) as described earlier gives compounds of type (1).

A compound of formula (I, G=H) may be prepared by the cyclisation of acompound of formula (N), wherein R is hydrogen or an alkyl group,preferably in the presence of an acid or base, and optionally in thepresence of a suitable solvent, by analogous methods to those describedby T. Wheeler, U.S. Pat. No. 4,209,532. The compounds of formula (N)have been particularly designed as intermediates in the synthesis of thecompounds of the Formula (I). A compound of formula (N) wherein R ishydrogen may be cyclised under acidic conditions, preferably in thepresence of a strong acid such as sulfuric acid, polyphosphoric acid orEaton's reagent, optionally in the presence of a suitable solvent suchas acetic acid, toluene or dichloromethane.

The following non-limiting examples provide specific synthesis methodsfor representative compounds of the present invention, as referred to inTables 1 & 2 below.

EXAMPLE 1:3-ACETYL-9-(2,6-DIMETHYL-4-PROP-1-YNYL-PHENYL)-3-AZASPIRO[5.5]UNDEC-4-ENE-8,10-DIONE(EXAMPLE A1)

Step 1: Synthesis of O3-tert-butyl O11-ethyl8,10-dioxo-3-azaspiro[5.5]undecane-3,11-dicarboxylate

Tert-Butyl 4-acetonylidenepiperidine-1-carboxylate (12.9 g, 54.0 mmol)was dissolved in ethanol (100 mL) and diethyl propanedioate (54.12 mmol)was added. The reaction mixture was treated with a solution of sodiumethoxide which had been prepared by the addition of sodium (54.1 mmol)to ethanol (30 ml) at room temperature. The reaction mixture was stirredat room temperature for 3 hours then heated to reflux for 1 hour. Uponcooling the reaction mixture was concentrated in vacuo to giveO3-tert-butyl O11-ethyl8,10-dioxo-3-azaspiro[5.5]undecane-3,11-dicarboxylate as an oil, whichwas used in the next step without further purification.

Step 2: Synthesis of tert-butyl8,10-dioxo-3-azaspiro[5.5]undecane-3-carboxylate

Crude O3-tert-butyl O11-ethyl8,10-dioxo-3-azaspiro[5.5]undecane-3,11-dicarboxylate from step 1 wasdissolved in aqueous NaOH (12M, 5 mL) and stirred for 5 hours. Thereaction mixture was acidified to pH 6 by the addition of conc HCl at 0°C., and extracted with EtOAc. The organics were dried and concentratedin vacuo to leave a yellow solid which on trituration yielded a palepink powder of tert-butyl8,10-dioxo-3-azaspiro[5.5]undecane-3-carboxylate. The aqueous layer wasfurther acidified to pH 2 by the addition of conc HCl and extracted withEtOAc. The organics were dried and concentrated in vacuo to leave a paleyellow solid which on trituration with ether gave a further batch ofpale yellow powder of tert-butyl8,10-dioxo-3-azaspiro[5.5]undecane-3-carboxylate (3.914 g, 13.91 mmol).1H NMR (400 MHz, CDCl₃, keto from only) 3.51-3.25 (m, 6H), 2.69-2.54 (m,4H), 1.47-1.43 (m, 9H), 1.44-1.39 (m, 4H).

Step 3: Synthesis of tert-butyl9-(4-bromo-2,6-dimethyl-phenyl)-8,10-dioxo-3-azaspiro[5.5]undecane-3-carboxylate

Tert-Butyl 8,10-dioxo-3-azaspiro[5.5]undecane-3-carboxylate (0.5 g, 1.8mmol) and DMAP (1.1 g, 8.9 mmol) were dissolved in chloroform (20 mL).The reaction mixture was stirred under nitrogen for 10 minutes andtoluene (5 mL) was added followed by[diacetoxy-(4-bromo-2,6-dimethyl-phenyl)plumbyl] acetate (1.2 g, 2.1mmol). The resulting suspension was heated under nitrogen at 75° C. for3 hours and then allowed to cool to room temperature. The reactionmixture was treated with 2 M HCl (50 mL) and white precipitate formed onstirring. The mixture was filtered and the organic phase was separatedand the aq layer was extracted with DCM. The combined organics weredried (MgSO4), evaporated and purified by flash column chromatography(gradient elution: 5-100% EtOAc:iso-hexane) to give tert-butyl9-(4-bromo-2,6-dimethyl-phenyl)-8,10-dioxo-3-azaspiro[5.5]undecane-3-carboxylate(0.51 g, 1.1 mmol). 1H NMR (400 MHz, CD₃OD) 7.25-7.10 (m, 2H), 3.54-3.43(m, 4H), 2.61-2.52 (m, 4H), 2.05-1.98 (m, 7H), 1.72-1.56 (m, 4H),1.48-1.39 (m, 9H).

Step 4: Synthesis of tert-butyl9-(2,6-dimethyl-4-prop-1-ynyl-phenyl)-8,10-dioxo-3-azaspiro[5.5]undecane-3-carboxylate

4-diphenylphosphanylbutyl(diphenyl)phosphane (32 mg, 0.075 mmol),dichlorobis(triphenylphosphine)palladium(II) (26 mg, 0.0373 mmol) andbut-2-ynoic acid (346 mg, 0.894 mmol) were placed into a microwave vial.A solution of tert-butyl9-(4-bromo-2,6-dimethyl-phenyl)-8,10-dioxo-3-azaspiro[5.5]undecane-3-carboxylate(0.346 g, 0.745 mmol) in DMSO (6 mL/mmol) was added followed by DBU(0.34 g, 2.24 mmol) and the reaction mixture was heated under microwaveirradiation at 110° C. for 45 minutes. The reaction was diluted with 2MHCl and extracted with DCM. The organics were dried and concentrated invacuo to leave an orange gum which purified by flash chromatography togive (gradient elution: 10-100% EtOAc in iso-hexane) tert-butyl9-(2,6-dimethyl-4-prop-1-ynyl-phenyl)-8,10-dioxo-3-azaspiro[5.5]undecane-3-carboxylate(0.193 g, 0.456 mmol). 1H NMR (400 MHz, CD₃OD) 7.07-6.93 (m, 2H),3.52-3.45 (m, 4H), 2.62-2.53 (m, 4H), 2.02-1.98 (m, 9H), 1.70-1.60 (m,4H), 1.51-1.42 (m, 9H).

Step 5: Synthesis of tert-butyl9-(2,6-dimethyl-4-prop-1-ynyl-phenyl)-8-methoxy-10-oxo-3-azaspiro[5.5]undec-8-ene-3-carboxylate

Tert-butyl9-(2,6-dimethyl-4-prop-1-ynyl-phenyl)-8,10-dioxo-3-azaspiro[5.5]undecane-3-carboxylate(0.235 g, 0.555 mmol) was suspended in acetone (10 mL) then potassiumcarbonate (1.500 equiv., 0.832 mmol) was added followed by iodomethane(5 equiv., 2.77 mmol). The reaction mixture was stirred at roomtemperature for 24 hours and was then concentrated on the rotavap andthen quenched by diluting cautiously into 2M HCl (effervescence) andextracted ×2 with EtOAc. The organics were dried and vacced down toleave an orange foam which was pre-absorbed onto silica and purified byflash chromatography to give tert-butyl9-(2,6-dimethyl-4-prop-1-ynyl-phenyl)-8-methoxy-10-oxo-3-azaspiro[5.5]undec-8-ene-3-carboxylate(0.18 g, 74%)

1NMR: 1H NMR (400 MHz, CDCl₃) δ=7.10-7.02 (m, 2H), 3.64-3.52 (m, 5H),3.39-3.29 (m, 2H), 2.64-2.47 (m, 4H), 2.02-1.97 (m, 9H), 1.74-1.55 (m,4H), 1.48-1.39 (m, 9H)

Step 6: Synthesis of tert-butyl9-(2,6-dimethyl-4-prop-1-ynyl-phenyl)-8-methoxy-4,10-dioxo-3-azaspiro[5.5]undec-8-ene-3-carboxylate

Tert-butyl9-(2,6-dimethyl-4-prop-1-ynyl-phenyl)-8-methoxy-10-oxo-3-azaspiro[5.5]undec-8-ene-3-carboxylate(0.1800 g, 0.4113 mmol) was taken up into nitromethane (2 mL) andbisacetoxy-iodobenzene (3 equiv., 1.234 mmol) was added. The reactionmixture was cooled to 0° C. and 2-hydroperoxy-2-methyl-propane was addeddropwise (4 equiv., 1.645 mmol), maintaining the temperature by the rateof addition. The reaction mixture was stirred for 4 hours at 0° C. andthen at room temperature for 36 hours then quenched by the addition ofsodium metabisulfite solution then extracted ×2 with EtOAc. The organicswere dried and vacced down to leave an orange foam which waspre-absorbed onto silica and purified by flash chromatography to givecrude tert-butyl9-(2,6-dimethyl-4-prop-1-ynyl-phenyl)-8-methoxy-4,10-dioxo-3-azaspiro[5.5]undec-8-ene-3-carboxylate(0.011 g, 0.024 mmol). 1NMR: 1H NMR (400 MHz, CDCl₃) δ=7.13-6.91 (m,2H), 3.85-3.60 (m, 2H), 3.56-3.48 (m, 3H), 2.67-2.49 (m, 6H), 2.07-1.98(m, 9H), 1.57-1.51 (m, 9H), 1.50-1.40 (m, 2H)

Step 7: Synthesis of tert-butyl9-(2,6-dimethyl-4-prop-1-ynyl-phenyl)-8-methoxy-10-oxo-3-azaspiro[5.5]undeca-4,8-diene-3-carboxylate

To a solution of tert-butyl9-(2,6-dimethyl-4-prop-1-ynyl-phenyl)-8-methoxy-4,10-dioxo-3-azaspiro[5.5]undec-8-ene-3-carboxylate(0.230 g, 0.509 mmol) in anhydrous toluene (2.00 mL) at −70° C. wasadded Super-Hydride (1M in THF) (1M, 0.560 mL, 0.560 mmol) dropwise.After stirring at −70° C. for 30 minutes N,N-Diisopropylethylamine(0.375 g, 2.90 mmol), 4,4-Dimethylaminopyridine (0.00124 g, 0.0102 mmol)and trifluoroacetic anhydride (0.128 g, 0.611 mmol) were added. Themixture was warmed to room temperature and stirred for 2 h. Water (4 mL)was added. The organic layer was separated and the aqueous layerextracted with EtOAc (×3). The combined organics were washed with brinesolution, dried over Na₂SO₄, filtered and concentrated to obtain crudematerial, which was purified by silica gel column chromatography usingEtOAc-Hexane as eluent to give the desired product.

1H NMR (CDCl₃, 400 MHz): δ=7.18-7.07 (2H), 6.93-6.76 (m, 1H), 4.85-4.80(m, 1H), 3.61-3.56 (5H), 2.70-2.62 (m, 2H), 2.56-2.52 (1H), 2.45-2.41(1H), 2.03-2.01 (9H), 1.86 (2H), 1.49 (s, 9H)

Step 8: Synthesis of9-(2,6-dimethyl-4-prop-1-ynyl-phenyl)-3-azaspiro[5.5]undec-4-ene-8,10-dionehydrochloride

Tert-butyl9-(2,6-dimethyl-4-prop-1-ynyl-phenyl)-8-methoxy-10-oxo-3-azaspiro[5.5]undeca-4,8-diene-3-carboxylate(400 mg, 0.918 mmol) was stirred at 0° C. in HCl in Dioxane (4M, 2.30mL, 9.18 mmol) for 1 h then stirred at RT overnight. Reaction mixturewas concentrated and triturated with pentane, decanted and dried toobtain product as a greenish solid, 300 mg. This is used crude in thenext step. LCMS (NH4OAc: CH3CN): M+H=322

Step 9: Synthesis of[3-acetyl-9-(2,6-dimethyl-4-prop-1-ynyl-phenyl)-10-oxo-3-azaspiro[5.5]undeca-4,8-dien-8-yl]acetate

9-(2,6-dimethyl-4-prop-1-ynyl-phenyl)-8-hydroxy-3-azaspiro[5.5]undeca-4,8-dien-10-onehydrochloride (195 mg, 0.545 mmol) was taken up in dichloromethane (10mL) and acetyl chloride (0.156 mL, 2.18 mmol was added at 0° C. followedby triethylamine (0.608 mL, 4.36 mmol) upon which all solids wentimmediately into solution. The reaction was stirred at room temperaturefor 1 h. The reaction mixture was diluted with DCM and washed withwater. The aqueous layer extracted with DCM (×2). The combined organicswere dried over Na₂SO₄, filtered and concentrated to obtain crudeproduct.

LCMS (NH4OAc: CH₃CN): M+H=406

Step 10: Synthesis of3-acetyl-9-(2,6-dimethyl-4-prop-1-ynyl-phenyl)-3-azaspiro[5.5]undec-4-ene-8,10-dione(Example A1)

[3-acetyl-9-(2,6-dimethyl-4-prop-1-ynyl-phenyl)-10-oxo-3-azaspiro[5.5]undeca-4,8-dien-8-yl]acetate was dissolved in methanol (10 mL) and to this was added K₂CO₃(0.181 g, 1.31 mmol). The reaction mixture was stirred at roomtemperature for 1 h and then concentrated and the residue diluted withwater, washed with EtOAc (×2). The combined organics were washed withbrine solution. The combined basic aqueous layers were acidified with 1NHCl and extracted with EtOAc (×3). The combined organics were dried overNa₂SO₄, filtered and concentrated to obtain crude material, which waspurified by prep-HPLC to give desired product as a white solid (69 mg).

1H NMR (400 MHz, Methanol-d4) δ=7.15 (d, 0.4H), 7.03 (s, 2H), 6.79 (d,0.7H), 5.17-5.10 (m, 1H), 3.74-3.73 (m, 2H), 2.64-2.49 (m, 4H), 2.18 (s,3H), 2.04-2.03 (6H), 1.99 (m, 4H), 1.90 (t, 1H)

Examples of herbicidal compounds of the present invention.

TABLE 1 CMP Structure NMR A1

1H NMR (400 MHz, Methanol-d4) δ = 7.15 (d, 0.4H), 7.03 (s, 2H), 6.79 (d,0.7H), 5.17-5.10 (m, 1H), 3.74-3.73 (m, 2H), 2.64-2.49 (m, 4H), 2.18 (s,3H), 2.04-2.03 (6H), 1.99 (m, 4H), 1.90 (t, 1H) A2

1H NMR (400 MHz, Methanol-d4) δ = 7.06- 6.98 (m, 2H), 3.43-3.36 (m, 2H),2.69-2.50 (m, 4H), 2.47-2.33 (m, 2H), 2.06-1.99 (m, 9H), 1.94- 1.84 (m,2H) A3

1H NMR (400 MHz, Methanol-d4) δ = 7.03- 7.01 (2H), 3.65-3.52 (4H),2.55-2.47 (4H), 2.12-2.03 (6H), 1.99- 1.98 (6H), 1.73-1.64 (m, 2H) A4

1H NMR (400 MHz, Methanol-d4) δ = 7.04 (s, 2H), 3.67 (t, J = 7.2 Hz,2HA), 3.57 (t, J = 7.2 Hz, 2HB), 3.52 (s, 2HB), 3.44 (s, 2HA), 2.65 (s,4H), 2.09-1.97 (m, 14H). A5

1H NMR (400 MHz, Acetonitrile-D3) δ = 7.14- 7.00 (m, 2H), 3.63- 3.55 (m,2H), 3.05-2.98 (m, 3H), 2.91-2.80 (m, 2H), 2.74-2.64 (m, 2H), 2.17-2.08(m, 2H), 2.04- 2.02 (m, 6H), 2.02- 2.00 (m, 3H) A6

1H NMR (400 MHz, Methanol-d4) δ = 7.03 (s, 2H), 3.50-3.37 (m, 4H), 2.59-2.45 (m, 4H), 2.05-1.97 (m, 9H), 1.88- 1.68 (m, 6H), 1.47 (s, 9H). A7

1H NMR (400 MHz, Methanol-d4) δ = 7.04- 7.00 (m, 2H), 3.55-3.49 (m, 2H),3.35 (s, 2H), 3.15-3.06 (m, 2H), 2.64 (s, 4H), 2.06-1.97 (m, 11H), 1.34(t, J = 7.4 Hz, 3H). A8

1H NMR (400 MHz, Methanol-d4) δ = 1H NMR (400 MHz, methanol) δ = 7.03(s, 2H), 3.46-3.37 (m, 4H), 3.06 (q, 2H), 2.58 (s, 4H), 2.04-1.97 (m,9H), 1.94-1.87 (m, 2H), 1.86- 1.76 (m, 4H), 1.30 (t, 3H) A9

1H NMR (400 MHz, Methanol) δ = 7.03 (d, J = 1.6 Hz, 2H), 3.59- 3.50 (m,4H), 2.61-2.47 (m, 4H), 2.12 (d, J = 2.1 Hz, 3H), 2.04-1.97 (m, 9H),1.96-1.69 (m, 6H). A10

1H NMR (400 MHz, Methanol-d4) δ = 7.03 (S, 2H), 2.64-2.62 (m, 5H),2.44-2.41 (t, 2H), 2.01-1.98 (10H), 1.95- 1.94 (t, 2H) A11

1H NMR (400 MHz, CDCl3) δ = 7.07 (s, 2H), 5.69 (br s, 1H), 3.43 (d, 1H),3.31 (d, 1H), 2.79 (s, 2H), 2.64 (s, 2H), 2.50 (t, 2H), 2.07-1.90 (m,11H), 1.86 (s, 3H) A12

1H NMR (400 MHz, Methanol-d4) δ = 7.02 (s, 2H), 4.14 (s, 2H), 3.71 (s,3H), 3.45 (s, 2H), 2.65-2.64 (d, 4H), 2.52- 2.49 (t, 2H), 2.01-1.95 (m,11H) A13

1H NMR (400 MHz, Methanol-d4) δ = 7.02 (s, 2H), 4.58-4.55 (m, 1H),3.66-3.52 (m, 1H), 2.81-2.67 (m, 3H), 2.43 (s, 2H), 2.67 (s, 2H),2.35-2.31 (m, 2H), 2.01- 1.98 (10H), 1.93 (s, 2H), 1.85-1.82 (m, 1H),1.71-1.70 (m, 1H), 1.55- 1.53 (m, 1H), 1.49-1.46 (m, 2H) A14

1H NMR (400 MHz, Methanol-d4) δ = 7.01 (s, 2H), 3.97-3.93 (m, 1H),3.82-3.79 (m, 1H), 2.95 (t, 1H), 2.67 (s, 2H), 2.39-2.35 (m, 4H),2.26-2.24 (m, 1H), 2.14- 2.11 (m, 1H), 2.02-1.92 (10H), 1.64-1.59 (m,1H), 1.44-1.38 (m, 1H), 1.24 (t, 1H) A15

1H NMR (400 MHz, Methanol-d4) δ = 7.13 (d, 0.4H), 7.02 (s, 2H), 6.69 (d,0.6H), 5.22 (d, 0.4H), 5.13 (d, 0.6H), 4.26 (s, 2H), 3.77-3.60 (m, 2H),3.45-3.37 (m, 3H), 2.63-2.45 (m, 4H), 2.05-1.85 (m, 11H) A16

1H NMR (400 MHz, Methanol-d4) δ = 7.54- 7.49 (m, 5H), 7.28 (br s, 0.3H)7.02 (s, 2H), 6.52- 6.49 (m, 0.7H), 5.36 (br s, 0.3H) 5.05-5.00 (m,0.7H), 3.89 (br s, 1.5H), 3.66 (br s, 0.5H), 2.69- 2.52 (m, 4H),2.11-1.84 (m, 11H) A17

1H NMR (400 MHz, Methanol-d4) δ = 7.12 (d, 1H), 7.04 (s, 2H), 5.07 (d,1H), 3.79-3.73 (m, 2H), 2.58 (q, 4H), 2.06-1.96 (m, 9H), 1.95- 1.88 (t,2H), 1.31 (s, 9H) A18

— A19

— A20

— A21

— A22

1H NMR (400 MHz, Methanol-d4) δ = 7.02 (s, 2H), 4.50-4.28 (m, 1H),3.60-3.56 (m, 1H), 3.43-3.40 (d, 0.4H), 3.20-3.18 (d, 0.6H), 2.74-2.68(m, 2H), 2.59-2.46 (m, 3H), 2.09-1.96 (m, 12H), 1.90-1.64 (m, 3H), 1.59-1.53 (m, 1H) Rotamers present A23

A24

A25

A26

A27

A28

A29

A30

A31

A32

A33

A34

A35

A36

A37

A38

A39

A40

A41

A42

A43

A44

A45

A46

A47

A48

1H NMR (400 MHz, Methanol-d4) δ = 8.61 (d, 1H), 7.98 (t, 1H), 7.69-7.67(m, 1H), 7.53 (t, 1H), 7.30 (d, 0.4H), 7.03-7.02 (m, 2H), 6.61 (d,0.6H), 5.40 (d, 0.4H), 5.03 (d, 0.6H), 3.97-3.89 (m, 1.2H), 3.75-3.68(m, 0.8H), 2.71-2.49 (m, 4H), 2.10-1.88 (m, 11H) Rotamers present A49

1H NMR (400 MHz, Methanol-d4) δ = 7.19- 7.10 (m, 1H), 7.03 (s, 2H), 5.15(d, 1H), 3.98- 3.92 (m, 1H), 3.74-3.67 (m, 1H), 2.63-2.49 (m, 4H),2.08-1.86 (m, 12H), 0-93-0.88 (m, 4H) A50

1H NMR (400 MHz, Methanol-d4) δ = 7.15 (d, 0.5H), 7.04 (s, 2H), 6.67 (d,0.5H), 6.50 (t, 1H), 5.20 (dd, 1H), 4.73- 4.72 (m, 2H), 3.96-3.61 (m,2H), 2.68-2.50 (m, 4H), 2.05-1.88 (m, 11H) A51

1H NMR (400 MHz, Methanol-d4) δ = 7.12 (d, 0.4H), 7.03 (s, 2H), 6.64 (d,0.6H), 5.22 (dd, 1H), 3.80-3.63 (m, 2H), 3.32-3.27 (m, 2H), 2.62- 2.48(m, 4H), 2.05-1.87 (m, 11H) Rotamers present A52

1H NMR (400 MHz, Methanol-d4) δ = 7.88 (s, 1H), 7.04-6.96 (m, 2H), 4.55(s, 1H), 3.72- 3.66 (m, 1H), 3.14-3.03 (m, 1H), 2.59-2.38 (m, 4H),2.06-1.89 (m, 11H) A53

1H NMR (400 MHz, Methanol-d4) δ = 7.03 (s, 2H), 6.81 (d, 1H), 5.96 (br,1H), 4.88 (d, 1H), 3.58-3.51 (m, 2H), 2.54 (q, 4H), 2.03 (d, 6H), 1.98(s, 3H), 1.92- 1.87 (m, 2H), 1.35 (s, 9H) A54

1H NMR (400 MHz, Methanol-d4) δ = 7.02 (s, 2H), 6.79-6.58 (m, 1H), 5.14(d, 1H), 3.72- 3.65 (m, 2H), 2.58 (q, 4H), 2.05-1.92 (m, 11H), 1.24 (s,9H) A55

1H NMR (400 MHz, Methanol-d4) δ = 7.03 (s, 2H), 6.59 (d, 1H), 5.02 (d,1H), 3.65-3.58 (m, 2H), 3.17 (q, 2H), 2.58 (q, 4H), 2.02-1.95 (m, 11H),1.31 (t, 3H) A56

1H NMR (400 MHz, Methanol-d4) δ = 7.12 (d, 0.4H), 7.04 (s, 2H), 6.86 (d,0.6H), 6.54 (t, 1H), 5.39 (d, 0.4H), 5.24 (d, 0.6H), 3.84-3.76 (m, 2H),2.69-2.50 (m, 4H), 2.07-1.95 (m, 11H) A57

1H NMR (400 MHz, Methanol-d4) δ = 8.69 (d, 1H), 8.20 (d, 1H), 8.03 (t,1H), 7.67-7.62 (m, 1H), 7.03 (s, 2H), 6.98-6.73 (m, 1H), 5.22 (d, 1H),3.85-3.79 (m, 2H), 2.59 (q, 4H), 2.05- 1.96 (m, 11H) A58

1H NMR (400 MHz, Methanol-d4) δ = 7.03 (s, 2H), 4.58 (br s, 1H),4.42-4.17 (m, 1H), 3.70 (br s, 1H), 3.42 (br s, 1H), 2.72 (br s, 2H),2.52 (d, 1H), 2.37 (d, 1H), 2.11 (s, 3H), 2.01- 1.98 (m, 9H), 1.89-1.60(m, 3H), 1.41-1.12 (m, 3H) A59

1H NMR (400 MHz, Methanol-d4) δ = 7.03 (s, 2H), 3.79-3.47 (m, 4H), 2.88(d, 1H), 2.66- 2.48 (m, 2H), 2.45-2.37 (m, 1H), 2.10 (s, 3H), 2.07-1.93(m, 9H), 1.88- 1.70 (m, 1H), 1.62-1.45 (m, 2H). 1.06-0.97 (m, 3H) A60

A61

A62

A63

1H NMR (400 MHz, Methanol-d4) δ = 7.02 (s, 2H), 4.11 (s, 2H), 3.47 (s,2H), 2.74-2.60 (m, 4H), 2.51 (t, 2H), 2.04-1.92 (m, 11H) A64

1H NMR (400 MHz, Methanol-d4) δ = 7.01 (s, 2H), 4.02 (s, 2H), 3.42 (s,2H), 2.73 (s, 3H), 2.65-2.57 (m, 4H), 2.51 (t, 2H), 2.05-1.94 (m, 11H)A65

1H NMR (400 MHz Methanol-d4) δ = 7.00 (s, 2H), 4.24 (s, 2H), 3.41 (s,2H), 3.03 (s, 3H), 2.93 (s, 3H), 2.65- 2.53 (m, 4H), 2.50 (t, 2H),2.04-1.95 (m, 11H) A66

A67

TABLE 2 CMP Structure NMR P1

1H NMR (400 MHz, Methanol-d4) δ = 7.01 (s, 2H), 3.66-3.45 (m, 4H), 2.75(d, 2H), 2.66- 2.51 (m, 2H), 2.12 (d, 3H), 2.06-1.67 (m, 18H) P2

1H NMR (400 MHz, Methanol-d4) δ = 7.04- 6.95 (m, 2H), 3.87-3.71 (m, 2H),2.89-2.74 (m, 3H), 2.73-2.60 (m, 3H), 2.52-2.44 (m, 3H), 2.12- 2.05 (m,1H), 2.04- 1.99 (m, 9H), 1.99-1.90 (m, 1H), 1.88-1.81 (m, 2H) P3

1H NMR (400 MHz, chloroform) δ = 7.11- 7.06 (m, 2H), 3.73-3.56 (m, 7H),2.91-2.76 (m, 2H), 2.75-2.60 (m, 2H), 2.08-2.02 (m, 14H)

BIOLOGICAL EXAMPLES

Seeds of a variety of test species are sown in standard soil in pots(Lolium perenne (LOLPE), Setaria faberi (SETFA), Alopecurus myosuroides(ALOMY), Echinochloa crus-galli (ECHCG), Avena fatua (AVEFA)). Aftercultivation for one day (pre-emergence) or after 8 days cultivation(post-emergence) under controlled conditions in a glasshouse (at 24/16°C., day/night; 14 hours light; 65% humidity), the plants are sprayedwith an aqueous spray solution derived from the formulation of thetechnical active ingredient in acetone/water (50:50) solution containing0.5% Tween 20 (polyoxyethelyene sorbitan monolaurate, CAS RN 9005-64-5).Compounds are applied at 250 g/h. The test plants are then grown in aglasshouse under controlled conditions in a glasshouse (at 24/16° C.,day/night; 14 hours light; 65% humidity) and watered twice daily. After13 days for pre and post-emergence, the test is evaluated for thepercentage damage caused to the plant. The biological activities areshown in the following table on a five-point scale (5=80-100%; 4=60-79%;3=40-59%; 2=20-39%; 1=0-19%).

TABLE B1 LOLPE SETFA ALOMY ECHCG AVEFA Compound PRE POST PRE POST PREPOST PRE POST PRE POST A2 4 4 5 5 3 3 3 5 3 4 A3 2 5 3 5 2 5 2 5 3 5 A45 5 5 5 5 5 5 5 5 5 A5 5 5 5 5 3 5 5 5 3 4 A6 5 5 5 5 4 5 5 5 4 4 A7 5 55 5 5 5 5 5 5 5 A8 5 5 5 5 5 5 5 5 5 5 A9 5 5 5 5 5 5 5 5 5 5 A10 5 5 55 5 5 5 5 5 5 A11 5 5 5 5 5 5 5 5 3 5 A12 5 5 5 5 5 2 5 5 3 5 A13 5 5 55 5 5 5 5 5 5 A14 5 5 5 5 5 5 5 5 5 5 A15 5 5 5 5 5 5 5 5 5 5 A48 5 5 55 5 5 5 5 5 5 A49 5 5 5 5 5 5 5 5 5 5 A50 5 5 5 5 5 5 5 5 5 5 A51 5 5 55 5 5 5 5 5 5 A53 5 5 5 5 5 5 5 5 2 4 A54 5 5 5 5 5 5 5 5 5 5 A55 5 5 55 5 5 5 5 5 5 A56 5 5 5 5 5 5 5 5 5 5 A57 5 5 5 5 5 5 5 5 4 5 A58 5 5 55 5 5 5 5 5 5 A59 5 5 5 5 5 5 5 5 5 5 P1 5 5 5 5 5 5 5 5 5 5 P2 5 5 5 55 5 5 NT 5 5 P3 5 5 5 5 5 5 5 5 4 5 NT = Not Tested

1. A compound of Formula (I)

wherein R¹ is selected from methyl, ethynyl, 1-propynyl, phenyl and a 5or 6 membered heteroaryl which comprises one or two nitrogenheteroatoms, said phenyl and heteroaryl optionally substituted by one ortwo R¹⁵ substituents; R² is methyl, ethyl, methoxy or chloro; R³ isselected from the group consisting of methyl, ethyl, methoxy and chloro;R⁴ is selected from the group consisting of D1, D2, D3, D4, D5, D6, D7,D8, D9, D10, D11, D12, D13, D14, D15, D16, D17, D18, D19, D20, D21 D22,D23, D24, D25, D26, D27, D28, D29, D30, D31, D32, D33, D34, D35 and D36:

Y is selected from the group consisting of O, CR²⁷R²⁸ and N—R²⁹; Z is Nor CH; R^(4c) is selected from the group consisting of hydrogen,C₁-C₄alkyl, C₁-C₄alkoxy-, C₁-C₄haloalkyl, —C(═O)C₁-C₄alkyl,—C(═O)C₁-C₄haloalkyl, —S(O)_(n)C₁-C₆alkyl, —S(O)_(n)C₁-C₆haloalkyl,—S(O)_(n)—(CH₂)_(n)—C₃-C₆cycloalkyl, —S(O)_(n)C(R¹¹)R¹²R¹³, —C(O)H,—C(O)—(CH₂)_(n)—C₃-C₆cycloalkyl, —C(O)C(R¹¹)R¹²R¹³, —C(O)C₂-C₄alkenyl,—C(O)(CR⁹R¹⁰)CN, —C(O)(CR⁹R¹⁰)(CR⁹R¹⁰)CN, —C(O)CH₂C(O)—C₁-C₆alkyl,—C(O)CH₂OC(O)—C₁-C₆alkyl, —C(O)OC₁-C₆alkyl, —C(O)OC₁-C₆haloalkyl,—C(O)(CH₂)_(n)S(O)_(n)C₁-C₆alkyl, —C(O)C₁-C₃alkoxyC₁-C₆alkyl,—C(O)C₁-C₃alkoxyC₂-C₆alkenyl, —C(O)C₁-C₃alkoxyC₂-C₆alkynyl,—C(O)C₁-C₃alkoxyC₁-C₆haloalkyl, —C(O)C₁-C₃alkoxyC₃-C₆cycloalkyl,—C(O)OC₁-C₃alkoxyC₁-C₆alkyl, —C(O)C₁-C₃alkoxyC₁-C₃alkoxyC₁-C₆alkyl,—C(O)(CH₂)_(n)NR⁵R⁶, —C(O)—(CH₂)_(n)—NR⁷C(O)R⁸,—C(O)—(CH₂)_(n)—O—N═CR⁵R⁵, —CN, —S(O)₂NR¹⁶R¹⁷, —S(O)(═NR¹⁸)R¹⁹,—C(O)C(O)R²⁰, —C(O)C(R²³)═N—O—R²⁴ or —C(O)C(R²³)═N—NR²⁵R²⁶,—(CH₂)_(n)-phenyl, —C(O)—(CH₂)_(n)-phenyl, —S(O)_(n)—(CH₂)_(n)-phenyl,-heterocyclyl, —C(O)—(CH₂)_(n)-heterocyclyl,—C(O)(CH₂)_(n)O—(CH₂)_(n)-heterocyclyl,—S(O)_(n)—(CH₂)_(n)-heterocyclyl, wherein each heterocyclyl is a 5- or6-membered heterocyclyl which may be aromatic, saturated or partiallysaturated and can contain from 1 to 4 heteroatoms each independentlyselected from the group consisting of oxygen, nitrogen and sulphur, andwherein said heterocyclyl or phenyl groups are optionally substituted byone, two or three substituents independently selected from the groupconsisting of C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₂-C₃alkenyl,C₂-C₃alkynyl, halogen, cyano and nitro; R⁵ is selected from the groupconsisting of hydrogen and C₁-C₆ alkyl; R⁶ is selected from the groupconsisting of hydrogen, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl,C₁-C₆haloalkyl, hydroxyl-, C₁-C₆alkoxy, C₃-C₆ cycloalkyl,—C₁-C₄alkoxyC₁-C₆alkyl, —C₁-C₃alkoxyC₁-C₆haloalkyl,—(CR⁹R¹⁰)C₁-C₆haloalkyl, —(CR⁹R¹⁰)C(O)NR⁵R⁵, phenyl, -pyridyl, whereinthe phenyl and pyridyl are optionally substituted by one, two or threesubstituents independently selected from the group consisting of C₁-C₃alkyl, C₁-C₃ haloalkyl, C₁-C₃ alkoxy, C₂-C₃ alkenyl, C₂-C₃ alkynyl,halogen, cyano and nitro; or R⁵ and R⁶ together form —CH₂CH₂OCH₂CH₂—;and R⁷ is selected from the group consisting of hydrogen and C₁-C₆alkyl; R⁸ is selected from the group consisting of hydrogen, C₁-C₆alkyl, C₁-C₆ alkoxy, C₃-C₆ cycloalkyl, phenyl, -pyridyl, wherein thephenyl and pyridyl are optionally substituted by one, two or threesubstituents independently selected from the group consisting of C₁-C₃alkyl, C₁-C₃ haloalkyl, C₁-C₃ alkoxy, C₂-C₃ alkenyl, C₂-C₃ alkynyl,halogen, cyano and nitro; R⁹ is hydrogen or methyl; R¹⁰ is hydrogen ormethyl; or R⁹ and R¹⁰ together form —CH₂CH₂—; and R¹¹ is hydrogen ormethyl; R¹² is selected from the group consisting of hydrogen, C₁-C₆alkyl, hydroxyl and C₁-C₆ alkoxy-; R¹³ is selected from the groupconsisting of hydrogen, C₁-C₆ alkyl, hydroxyl and C₁-C₆ alkoxy; or R¹²and R¹³ together form —CH₂—X—CH₂—; and X is selected from the groupconsisting of O, S and N—R¹⁴; R¹⁴ is selected from the group consistingof hydrogen, C₁-C₃ alkyl and C₁-C₃ alkoxy-; R¹⁵ is independentlyselected from the group consisting of C₁-C₄ alkyl, C₁-C₄ haloalkyl,cyano and halogen; R¹⁶ is hydrogen or C₁-C₆alkyl; and R¹⁷ is selectedfrom the group consisting of hydrogen, C₁-C₆alkyl, C₃-C₆cycloalkyl,C₁-C₆ alkoxy-C₁-C₃alkyl-, —C(O)C₁-C₆alkyl, —C(O)OC₁-C₆alkyl and CH₂CN;or R¹⁶ and R¹⁷ together form —CH₂CH₂OCH₂CH₂—, —CH₂CH₂S(O)₂CH₂CH₂—; R¹⁸is hydrogen or C₁-C₆alkyl; R¹⁹ is selected from the group consisting ofhydrogen, C₁-C₆ alkyl, C₁-C₆ alkoxy, C₃-C₆cycloalkyl, phenyl, -pyridyl,wherein the phenyl and pyridyl are optionally substituted by one, two orthree substituents independently selected from the group consisting ofC₁-C₃ alkyl, C₁-C₃ haloalkyl, C₁-C₃ alkoxy, C₂-C₃ alkenyl, C₂-C₃alkynyl, halogen, cyano and nitro; R²⁰ is selected from the groupconsisting of C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy-, C₁-C₆haloalkoxy,—NR²¹R²², phenyl and -pyridyl, wherein the phenyl and pyridyl areoptionally substituted by one, two or three substituents independentlyselected from the group consisting of C₁-C₃ alkyl, C₁-C₃ haloalkyl,C₁-C₃ alkoxy, C₂-C₃ alkenyl, C₂-C₃ alkynyl, halogen, cyano and nitro;R²¹ is selected from the group consisting of hydrogen, C₁-C₆ alkyl,C₁-C₆ alkoxy, C₁-C₆alkoxyC₁-C₃alkyl-, C₃-C₆ cycloalkyl, C₁-C₆haloalkyl-and C₁-C₆haloalkoxy-, —C(O)C₁-C₆alkyl, phenyl, -pyridyl, wherein thephenyl and pyridyl are optionally substituted by one, two or threesubstituents independently selected from the group consisting of C₁-C₃alkyl, C₁-C₃ haloalkyl, C₁-C₃ alkoxy, C₂-C₃ alkenyl, C₂-C₃ alkynyl,halogen, cyano and nitro; R²² is hydrogen or C₁-C₆alkyl; or R²¹ and R²²together form —CH₂CH₂OCH₂CH₂—; R²³ is selected from the group consistingof hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy- andC₁-C₆haloalkoxy-; R²⁴ is selected from the group consisting of hydrogen,C₁-C₆alkyl, C₁-C₆alkoxyC₁-C₃alkyl-, C₃-C₆cycloalkyl, —CH₂CN,tetrahydropyranyl-, phenyl and -pyridyl, wherein the phenyl and pyridylare optionally substituted by one, two or three substituentsindependently selected from the group consisting of C₁-C₃alkyl,C₁-C₃haloalkyl, C₁-C₃alkoxy, C₂-C₃alkenyl, C₂-C₃alkynyl, halogen, cyanoand nitro; R²⁵ is hydrogen or C₁-C₆ alkyl; R²⁶ is hydrogen or C₁-C₆alkyl; R²⁷ is hydrogen or C₁-C₄alkyl; R²⁸ is hydrogen or C₁-C₄alkyl; R²⁹is selected from the group consisting of hydrogen, C₁-C₄alkyl,C₁-C₄alkoxy-, C₁-C₄haloalkyl, —C(═O)C₁-C₄alkyl, —C(═O)C₁-C₄haloalkyl;and R³⁰ and R³¹ are independently selected from the group consisting ofhydrogen, halogen, C₁-C³ alkyl, C₁-C₃ haloalkyl and C₁-C₃alkoxy butwherein both R³⁰ and R³¹ are not hydrogen; G is selected from the groupconsisting of hydrogen, —(CH₂)_(n)—R^(a), —C(O)—R^(a),—C(O)—(CR^(c)R^(d))_(n)—O—R^(b), —C(O)—(CR^(c)R^(d))_(n)—S—R^(b),—C(O)NR^(a)R^(a), —S(O)₂—R^(a) and C₁-C₈alkoxy-C₁-C₃alkyl-; R^(a) isindependently selected from the group consisting of hydrogen,C₁-C₈alkyl, C₁-C₃haloalkyl, C₂-C₈alkenyl, C₂-C₈alkynyl, C₃-C₆cycloalkyl,heterocyclyl and phenyl wherein said heterocyclyl and phenyl groups areoptionally substituted by one, two or three substituents independentlyselected from the group consisting of C₁-C₃alkyl, C₁-C₃haloalkyl,C₁-C₃alkoxy, C₂-C₃alkenyl, C₂-C₃alkynyl, halogen, cyano and nitro; R^(b)is selected from the group consisting of C₁-C₈alkyl, C₁-C₃haloalkyl,C₂-C₈alkenyl, C₂-C₈alkynyl, C₃-C₆ cycloalkyl, heterocyclyl and phenylwherein said heterocyclyl and phenyl groups are optionally substitutedby one, two or three substituents independently selected from the groupconsisting of C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₂-C₃alkenyl,C₂-C₃alkynyl, halogen, cyano and nitro; R^(c) is hydrogen or C₁-C₃alkyl; R^(d) is hydrogen or C₁-C₃ alkyl; and n is independently 0, 1 or2; or an agriculturally acceptable salt thereof.
 2. A compound accordingto claim 1, wherein R¹ is 1-propynyl.
 3. A compound according to claim1, wherein R² is methyl.
 4. A compound according to claim 1, wherein R³is methyl.
 5. A compound according to claim 1, wherein R⁴ is D4 or D6.6. A compound according to claim 1, wherein R^(4c) is selected from thegroup consisting of —C(═O)C₁-C₄alkyl, —S(O)_(n)C₁-C₆alkyl,—C(O)C₁-C₃alkoxyC₁-C₆alkyl and —C(═O)phenyl.
 7. A compound according toclaim 1, wherein R^(4c) is —C(═O)C₁-C₄alkyl.
 8. A compound according toclaim 1, wherein G is hydrogen.
 9. A compound according to claim 1,wherein G is —C(O)C₁-C₆alkyl.
 10. A compound according to claim 1,wherein G is —C(O)—O—C₁-C₆alkyl.
 11. A herbicidal composition comprisinga compound of Formula (I) according to claim 1 and an agriculturallyacceptable formulation adjuvant.
 12. A herbicidal composition accordingto claim 11, further comprising at least one additional pesticide.
 13. Aherbicidal composition according to claim 12, wherein the additionalpesticide is a herbicide or herbicide safener.
 14. A method ofcontrolling weeds at a locus comprising application to the locus of aweed controlling amount of a composition according to claim
 1. 15. Useof a compound of Formula (I) as defined in claim 1 as a herbicide.